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A first date can be stressful, painful, amazing, magical, and/or horrifying. Sometimes, if the date’s gone well, you’re left wondering whether/not there will be a second. Let me leave you with a few sure signs that you’ll be seeing each other again.

He takes the train 45 minutes to see you.

He buys you a box of chocolates before the end of your date.

He buys you a giant bottle of whiskey to commemorate your date since you spent the day drinking whiskey.

He books a hotel room so he can stay with you a little longer.

You end up topless in his hotel room.

You’ll wind up on a second date in the next few weeks. You’ll probably want to shave your legs for that date…

I’m exhausted from Tindering and dating. Flirting with the world, coming up with crafty messages, figuring out what bra to wear and whether/not I should wear flats, and trying to pretend like I don’t care that #4 is being weird is enough to tire anyone out!

Two dates on Saturday. Two. Almost a third, but he waited too late to text me (more about him later).

I’ve not really had a date like this one before. Usually I go on dates because I think there’s potential for something with someone. In some cases we establish afterward that perhaps it’s not going to be long term, ala #4. At least by that point we already know there’s some chemistry. Prior to meeting Civil Servant we agreed it would be casual, so this was more of a formality to determine whether or not we had a spark. What added to the awkwardness, is there was zero booze involved. Coffee is great and all, but it doesn’t quite give you that faux confidence/courage that alcohol can give you. We shared Tinder stories, talked about awful hook ups, and about random other stuff. Here’s what I found out about him: he’s from the area, does policy work for the government, oldest of 6 kids, was on the verge of engagement when his relationship fell to shit, has a hot body, and a hell of a smile.

Was their heat? Yes there was. Someone I’d want to date long term? He’d bore me, wouldn’t challenge me (in a good way) enough. He double checked my age and told me I looked great and said, “you’re very attractive.” I’d like to send a shout out to genetics, a 30 pound weight loss, my J. Crew jeans that accentuate my backside, and a button down top that accentuated the girls (but not too much). My Tinder profile is clever and I mention I’m terrible when it comes to house repairs and I was hoping to find a handyman on Tinder. He said he could help and he’d bring his toolbox over and he’d take care of the little repairs around the house. He was dead serious. Adorable. Hawt.

He had his phone and I noticed he was getting a lot of text messages. At 2:15 I announced he had somewhere to be and we should wrap it up. He walked me to my car and said, “I’d really like to see you again. I think we’d have a lot of fun.” We both had plans for the night and agreed it would be fun to meet up sometime. That’s code for “get naked at my house.” He said he’d remember his toolbox. We should have made out – just that final chemistry test – but we didn’t.

The following text exchange proceeded.

Me: That was fun. You know how to find me. Don’t worry about the toolbox, I’m sure we can find something better to do. 😉 Enjoy going out with your friends tonight.

Him: Agreed 🙂 On both fronts 😘. Have fun with yours.

My text game was strong. He text messaged me yesterday.

Verdict: Civil Servant is a go. I’ve penciled him in for Thursday night. 🍆

Saturday Date 2: Fly Boy (#8)

A few days ago I matched with this guy on Tinder who was HILARIOUS. He had me doubled over, crying from his silly messages. Of course I had to whip my phone out and share the messages with my friend who agreed he was funny. He’s in Baltimore for a few months before being sent overseas for some assignment. After an afternoon of text messaging, he said, “I’ve melted my brain playing too many video games. Let’s go be awesome.” Clever. I bit.

The plan was we’d meet up for a few drinks and then go find somewhere fun to go. I picked a low key place that has great food and drinks that are the bomb. I got there first, like usual. When he walked in, or more like sauntered in, I thought, “oh no. I think he likes boys.” Okay, reset. We’re going to be friends. Fine. He’s funny, and I love funny friends. We spent about 5 hours together, even went bowling afterward, and it was a fun night. Here are a few things I found out about him: he was raised Mormon, married for 8 years, and had 15 tattoos. He was not conservative in the least.

One of the things I love to do when I’m on a Tinder date is ask about the stories. I love hearing about the great dates and the terrible ones. The crazy girls. All of it. So I asked Fly Boy about his stories. He had nothing to share. He said he could always tell what the girl wanted in the early stages, and if it was too risque, he’d shoot it down and unmatch them. Bummer. No stories.

We ended the date with a hug in the car. I would have died from shock if he had tried anything. Also, ew, because we had no chemistry.

Verdict: Fly Boy is a no go. I’d love to set him up with one of my gay friends.

Meeting Civil Servant at 1:00. Have I mentioned lately he’s 12 years younger than I am?

Why limit the distractions to just one guy? Heading out for another date tonight. Not a booty call this time. An actual date. We’re going for drinks and then for bowling or indoor mini golf. He’s really funny, like I double over laughing at his texts.

We had made arrangements to meet at a cool restaurant downtown that I’d been dying to try. He arrived before I did and when I walked in I was happy to see that he was a bit cuter than his pics. He was also a bit shorter than I thought and with my amazing boots I was probably an inch taller than he was. Whatever, no bigs, figured I’d never have to wear heels again – I love flats. #6 was in a bit of a panic when I got there because he’d realized he’d left his wallet in the back of the uber. In some respects it worked out well because the problem solving mode we had to go into helped us get past any nervousness.

Wallet in hand, we were able to sit down and enjoy our drinks. The drink menu was the bomb and sitting at the bar we were able to watch all the madness in the restaurant. I’ve come to the conclusion that sitting at the bar is way better than sitting at a table because you’ve got a better chance of reading body language, and if they have hot arms and you want to touch them, it makes it easier.

For those of you who voted in the poll as to whether/not I should give him a birthday card (his birthday was the night before), “yes” was the right answer. He loved the card and was touched that I’d even thought to do that. I’m a kind person, god damn it (someone tell #4). Let me thank NONE of you for telling me what I should write in his birthday card. Really helpful. No really, thank you to no one. In the card I’d written that I’d handle first round of drinks and he told me absolutely not. When he got up to go to the bathroom I closed out the tab on the first round because I knew he’d fight me.

I had really low expectations going into the date. In our messaging he was making me do a whole lot of work and the conversation wasn’t flowing. In person, I was getting all sorts of right signals and the conversation was smooth. He shared some fun Tinder/OKC stories, asked questions about me, was a good flirt, and fun company. As I did the previous night on my date with #5, I got up at one point to go to the bathroom just so he could see how amazing I looked in my outfit. Yes, I wore the damn one as the previous date. No, I don’t have a problem with doing that. The outfit was banging. I may start wearing it everyday.

Three hours (and three drinks) went by in the blink of an eye. “I don’t know what I was expecting tonight, but I have to say I’m pleasantly surprised,” he told me. He said he thought I was smart and very attractive and that he’d love to see me again. Likewise. So promising! It was a great first date. Not quite as spicy as the first one with #4, missing some of the chemistry, but definitely worth another date.

I messaged him when I got home and gave him my number. Text message sent from him 5 minutes later. Good morning texts on Wednesday and Thursday – some witty banter the rest of the days. And yesterday he asked me out again. I said yes, of course I said yes, because he’s cute and funny and we have some chemistry and why the hell not?

Date #6 tonight. Don’t have high hopes, talking to him is a bit like pulling teeth. Feels like I’m doing all the work. I ask him questions, he responds. Ask him more questions, he responds again. Not a whole lot of back and forth. I can only imagine what tonight will be like. If it’s like the exchange in email, guessing tonight I will pretend I’m a professional interviewer and will get him to just tell me some good stories.

Assuming actually has good stories…Bit of a wet noodle maybe?

Know what would be amazing? If date #6 turned into date #sex. Hey-o! I made a lolz. Because six and sex sound similar. You chuckled. Admit it.

Anyway, bought him the birthday card – a benign card that wouldn’t be over the top. So what should I write in it? Help a sister out and put your thoughts in the comments. Don’t leave me hanging, yo.